EP0120305A1 - Verfahren zur Herstellung von gemischten aliphatisch-aromatischen Polycarbodiimiden - Google Patents
Verfahren zur Herstellung von gemischten aliphatisch-aromatischen Polycarbodiimiden Download PDFInfo
- Publication number
- EP0120305A1 EP0120305A1 EP84101922A EP84101922A EP0120305A1 EP 0120305 A1 EP0120305 A1 EP 0120305A1 EP 84101922 A EP84101922 A EP 84101922A EP 84101922 A EP84101922 A EP 84101922A EP 0120305 A1 EP0120305 A1 EP 0120305A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- aromatic
- aliphatic
- mono
- diisocyanate
- diisocyanates
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/02—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/02—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only
- C08G18/025—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only the polymeric products containing carbodiimide groups
Definitions
- This invention pertains to mixed aliphatic/aromatic polycarbodiimides and more particularly to a method for their preparation.
- polycarbodiimides as the crosslinker for well-known carboxylated latexes has been demonstrated to provide a requisite combination of control as well as rapid reaction.
- polycarbodiimides useful as crosslinkinq aqents it was found that aliphatic polycarbodiimides were very useful.
- the raw materials used to prepare the aliphatic materials are quite expensive.
- aromatic isocyanates used to prepare aromatic polycarbodiimides were considerably less expensive.
- aromatic polycarbodiimides failed to yield acceptable rates and degree of crosslinking.
- a co-polycarbodiimide containing the combination of both aliphatic and aromatic constituents formed by a proper mixture of aliphatic and aromatic isocyanates would yield the requisite crosslinking rate and acceptable cost parameters.
- Pressure and time are not critical. Although superatmospheric or sub-atmospheric pressures can be used, it is preferred to use atmospheric.pressures for economic reasons.
- temperatures of about 120°C to about 160°C can be used, it is preferred to use a range of about 120°C to about 140°C.
- catalytic amount is used herein to mean about 0.1 to about 0.8% by weight based on the total weight of isocyanates charged.
- catalysts can be used. Examples include the monoxidized phospholene as well as phospholene sulfide. Alternatives include derivatives derived by substituting on and for the phenyl groups attached to the phosphorus atom such as by an ethyl moiety. Additional substitutions on the cyclic phosphorus ring can be made by subsituting hydrogen, alkenyl, aryl, aralkyl, alkoxy, chlorine or bromine groups.
- Exemplary cycloaliphatic and saturated aliphatic mono and diisocyanates include:
- Exemplary aromatic mono and diisocyanates include:
- the molar ratios of all of the mono- to diisocyanate groups can range from about 2:1 to about 2:10 it is preferred to use ratios of about 2:1 to about 4:1.
- molar ratio of cycloaliphatic and/or saturated aliphatic isocyanate qroups to aromatic isocyanate groups can range from about 0.5:1 to about 2:1, it is preferred to use a range of about 0.75:1 to about 1.25:1.
- the method of the instant invention is preferably carried out in a non-reactive orqanic solvent such as, qlycol diesters or aliphatic esters each havinq about 8 to about 20 carbons, aromatic hydrocarbons having 6 to about 12 carbons, and the like.
- a non-reactive orqanic solvent such as, qlycol diesters or aliphatic esters each havinq about 8 to about 20 carbons, aromatic hydrocarbons having 6 to about 12 carbons, and the like.
- exemplary solvents include diethylene glycolether diacetate, dipropylene glycol dibutyrate, hexylene glycol diacetate, amyl acetate, butyl acetate, propryl propionate, ethyl butyrate toluene, o-, m- and p- xylene, benzene, diethyl benzene, and the like.
- a catalyst is employed preferably with an inert organic solvent and combinations of mono- and diisocyanates as desired to control the product polycarbodiimide molecular weight and functionality.
- the combination of two isocyanate moieties yields a carbodiimide group with evolution of carbon dioxide: It was found that during the preparation of mixed aliphatic and aromatic polycarbodiimides where the corresponding aliphatic and aromatic isocyanates are charged to the reactor together with solvent and catalyst that the rate of carbon dioxide evolution and carbodiimioe functionality formation decreased significantly during the process.
- the time of the decrease corresponded to the amount of aromatic isocyanate present due to the preferential reaction of aromatic isocyanate at the expense of the aliphatic isocyanate.
- the reactor raised to the reaction temperature and the aromatic isocyanate fed to the reactor last, a superior aliphatic/aromatic polycarbodiimide product was obtained.
- the product was superior to that obtained by charging all of the isocyanates to the reactor at the same time in having less discoloration and a much lower viscosity.
- any solvent can be used so long as the boiling point is sufficiently high to allow carbodiimide formation to take place and there are no active hydroqen groups on the solvent which could react with either the isocyanates or the product carbodiimides.
- the solvent can be placed in either the reactor charge or in the feed tank as preferred or split between them.
- Double Rub Test A piece of cheesecloth is saturated with methyl ethyl ketone, then rubbed on the substrate until penetration occurs. One back and forth rub is a double rub.
- Theoretical functionality An idealized value based on the theoretical structure assuminq pure materials with no side reactions.
- Example 2 To the apparatus of Example 1 were charged 83.4 g phenyl isocyanate, 155.6 g isophorone diisocyanate, 61.0 q toluene diisocyanate, 288 g hexylene glycol diacetate, and 12 g of 10% 3-methyl-1-phenyl-2-phospholene-1-oxide in xylene.
- the materials were heated with stirring and nitrogen sparqe to 145°C. After 10 hours reaction the material appeared close to completion of reaction but was extremely viscous and dark colored. Shortly thereafter the material solidified to a solid qel.
- Example 1 The apparatus of Example 1 was employed with the addition of a feed tank and pump. To the feed tank were charged 61.0 q toluene diisocyanate, 83.4 g phenyl isocyanate, and 285 g amyl acetate. To the reactor were charged 155.6 q isophorone diisocyanate and 15 g of a 10% solution of 3-methyl-l-phenyl-2-phospholene-l-oxide in xylene. The reactor was heated to 140°C with stirring and nitrogen sparge, and the material in the feed tank was added over a 5.5 hour period. After two additional hours of reaction the material was completed and cooled.
- the product had a viscosity of 0.5 Stoke (Gardner Bubble Viscometer) and a color of 5+ using a Gardner Hellige Comparator. Titration of the carbodiimide functionality gave a value of 9.75% by the procedure of Zaremko and Watts (Microchem. J. Symp. Ser., 2, 591(1962)).
- Example 3 The previous Example 3 was repeated with the exceptions being that a 5.25 hour feed time and a reaction temperature of 120°C was employed. The material required 21 hours to react to completion. Using the tests of Example 3, the product had a viscosity of 0.5 Stoke, a color rating of 5+, and a percent carbodiimide of 8.80.
- Example 3 Using the apparatus of Example 3, to the feed tank were charged 76.3 g phenyl isocyanate, 55.8 q. toluene diisocyanate, and 280 q. of hexylene glycol diacetate. The the reactor were charged 167.9 g bis-(4-isocyanatocyclohexyl)-methane and 20 g of a 10% solution of 3-methyl-l-phenyl-2-phospholene-1-oxide in xylene. A feed time of 3 hours was employed with a reaction temperature of 140°C. The reaction was completed after 26 hours. Analysis of the product as described in Example 3 gave a viscosity of 3.20 Stoke, a color rating of 12, and a percent carbodiimide of 8.78.
- Example 3 Using the apparatus of Example 3, to the feed tank were charged 140.3 q toluene diisocyanate and 280 g amyl acetate. To the reactor were charged 159.7 g butyl isocyanate and 20 g of 10% 3-methyl-l-phenyl-2-phospholene-l-oxide in xylene. A feed time of 3 hours was employed along with a reaction temperature of 140°C. The reaction required a total time of 5 hours for completion. Evaluation by the procedures in Example 3 gave a viscosity of less than 0.5 Stoke and a color ratinq of 7.
- Example 3 Using the apparatus of Example 3, to the feed tank were charqed 155.2 g phenyl isocyanate and 280 g amyl acetate and to the reactor were charged 144.8 q isophorone diisocyanate and 20 g of 10% 3-methyl-l-phenyl-2-phospholene-l-oxide in xylene. A reaction temperature of 140°C and a feed time of 3 hours were employed. The reaction required 22 hours for completion. Evaluation by the procedures in Example 3 gave a viscosity of less than 0.5 Stoke and a color rating of 5.
- Example 2 In the apparatus of Example 1 were charged 68.7 g butyl isocyanate, 231.2 g isophorone diisocyanate, 270 q amyl acetate, and 30 q of 10% 3-methyl-l-phenyl-2-phospholene-l-oxide in xylene. The mixture was heated with stirring at 140°C under a nitrogen sparge for 10 hours. Evaluation by the procedures in Example 3 qave a viscosity of less than 0.5 Stoke, a color rating of 3, and a percent carbodiimide of 9.79.
- Example 2 Into the apparatus of Example 1 were charged 93.9 g phenyl isocyanate, 206.1 q toluene diisocyanate, 270 q amyl acetate, and 30 g of a 10% 3-methyl-l-phenyl-2-phospholene-l-oxide. The mixture was heated with stirring under a nitrogen sparqe to 140°C. After 1 hour reaction time, the reaction was complete. Evaluation by the procedures of Example 3 qave a viscosity of less than 0.5 Stoke, a color rating of 7, and a percent carbodiimide of 11.36.
- LPCA 5011 described in U.S. 4,096,125 (20% CELLOSOLVE Acetate, 50% .phthallic anhydride, 15% NIAX polyol PCP-0300, 15% NIAX Polyol PCP-0301 to an approximate acid equivalent weight of 363) was used to prepare the following master batch:
- This well-stirred mix was placed in an oven at 50°C and found to gel in 2.3 hr.
- the master batch was additionally blended with the aromatic polycarbodiimide solution of Example 9.
- This mixture was placed in a 50°C oven and found to qel in 2 hours showing the surprising reactivity of the lower cost aliphatic/aromatic polycarbodiimide.
- Example 3 The polycarbodiimide solution of Example 3 was emulsified in water using the following materials and ratios:
- a base coating formulation was prepared as listed below:
- XAMA-7 Multifunctional aziridine crosslinker from Cordova Chemical.
- the final formulations were air-dried for two weeks at ambient temperature.
- the resultant films were evaluated for water swellinq by ambient temperature soakinq for two days and for tensile properties.
- a base hardboard primer formulation was prepared as shown below:
- the polycarbodiimide emulsion of Example 11 was employed to crosslink a water-borne pressure sensitive adhesive, UCAR 175.
- UCAR 175. a water-borne pressure sensitive adhesive
- the following formulations were prepared with the UCAR 175 beinq adjusted to pH 9 with triethylamine:
- the materials were applied to MYLAR tape and cured at 100°C for 30 min.
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Extrusion Moulding Of Plastics Or The Like (AREA)
- Organic Insulating Materials (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT84101922T ATE21386T1 (de) | 1983-02-24 | 1984-02-23 | Verfahren zur herstellung von gemischten aliphatisch-aromatischen polycarbodiimiden. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/469,434 US4487964A (en) | 1983-02-24 | 1983-02-24 | Method of making mixed aliphatic/aromatic polycarbodiimides |
US469434 | 1999-12-27 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0120305A1 true EP0120305A1 (de) | 1984-10-03 |
EP0120305B1 EP0120305B1 (de) | 1986-08-13 |
Family
ID=23863788
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP84101922A Expired EP0120305B1 (de) | 1983-02-24 | 1984-02-23 | Verfahren zur Herstellung von gemischten aliphatisch-aromatischen Polycarbodiimiden |
Country Status (8)
Country | Link |
---|---|
US (1) | US4487964A (de) |
EP (1) | EP0120305B1 (de) |
JP (1) | JPS59193916A (de) |
KR (1) | KR900008527B1 (de) |
AT (1) | ATE21386T1 (de) |
AU (1) | AU559037B2 (de) |
CA (1) | CA1213394A (de) |
DE (1) | DE3460449D1 (de) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1990014371A1 (en) * | 1989-05-26 | 1990-11-29 | Industrie Vernici Italiane S.P.A. | A quick-hardening coating composition |
EP0449143A2 (de) * | 1990-03-23 | 1991-10-02 | UNION CARBIDE CHEMICALS AND PLASTICS COMPANY INC. (a New York corporation) | Bei niedrigen Temperaturen aktive aliphatische/aromatische Polycarbodiimide |
EP0548815A2 (de) * | 1991-12-26 | 1993-06-30 | Nisshinbo Industries, Inc. | Tetramethylxylylene Carbodiimide |
EP0582983A1 (de) * | 1992-08-10 | 1994-02-16 | Nisshinbo Industries, Inc. | Verfahren zur Polycarbodiimidharzherstellung |
US5349087A (en) * | 1992-04-29 | 1994-09-20 | E. I. Du Pont De Nemours And Company | Carbodiimides and processes therefor |
EP0963283B2 (de) † | 1997-01-31 | 2010-12-08 | Magna Interior Systems Inc. | Verfahren zum herstellen von dekorativen kraftfahrzeuginnenverkleidungen mit vollständiger und lichtstabiler polyurethanelastomerbeschichtung |
DE19529631C5 (de) * | 1994-08-11 | 2012-05-03 | Nisshinbo Industries, Inc. | Verwendung eines oberflächenaktiven Mittels zur Oberflächenbehandlung von Verstärkungsmaterial, Verstärkungsmaterial mit einer mit dem genannten oberflächenaktiven Mittel behandelten Oberfläche und Verwendung des Verstärkungsmaterials |
CN108003313A (zh) * | 2017-12-21 | 2018-05-08 | 上海朗亿功能材料有限公司 | 一种嵌段型聚碳化二亚胺水性交联剂及其制备方法 |
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---|---|---|---|---|
US4820863A (en) * | 1986-03-31 | 1989-04-11 | Union Carbide Corporation | Surface active polycarbodiimides |
US5108653A (en) * | 1986-03-31 | 1992-04-28 | Union Carbide Chemicals & Plastics Technology Corporation | Surface active polycarbodiimides and their dispersions |
EP0277361A1 (de) * | 1986-12-30 | 1988-08-10 | Union Carbide Corporation | Oberflächenaktive Polycarbodiimide |
US5352831A (en) * | 1987-09-02 | 1994-10-04 | Ciba-Geigy Corporation | Oligomeric cyanoguanidines |
JP2796385B2 (ja) * | 1989-12-22 | 1998-09-10 | ミネソタ マイニング アンド マニユフアクチユアリング カンパニー | 撥水撥油処理剤 |
US5240811A (en) * | 1991-04-15 | 1993-08-31 | Ocg Microelectronic Materials, Inc. | Photogenerated polycarbodiimides from poly(tetrazole-5-thiones) and use in the preparation of coatings and deep-UV photoresists |
US5276096A (en) * | 1991-08-28 | 1994-01-04 | Basf Corporation | Two package coating composition comprising a polycarbodimide with improved rheology control |
US5936043A (en) | 1995-12-22 | 1999-08-10 | Rohm And Haas Company | Polymers crosslinkable with aliphatic polycarbodiimides |
KR100304475B1 (ko) * | 1996-01-18 | 2001-11-22 | 야마모토 히데키 | 방향족폴리카보디이미드및이로부터제조된필름 |
JP3518149B2 (ja) † | 1996-02-29 | 2004-04-12 | 日清紡績株式会社 | 水性プレコートメタル用塗料 |
JP3393752B2 (ja) * | 1996-04-26 | 2003-04-07 | 日清紡績株式会社 | エステル基を有する樹脂用の耐加水分解安定剤及び該安定剤によるエステル基を有する樹脂の耐加水分解安定化方法 |
US6362247B1 (en) | 2000-05-08 | 2002-03-26 | Rohm And Haas Company | Method of improving stability of aromatic polycarbodiimides |
US6566437B2 (en) | 2000-06-05 | 2003-05-20 | Rohm And Haas Company | Wear-resistant coating composition and method of producing a coating |
US6737489B2 (en) | 2001-05-21 | 2004-05-18 | 3M Innovative Properties Company | Polymers containing perfluorovinyl ethers and applications for such polymers |
US7045571B2 (en) * | 2001-05-21 | 2006-05-16 | 3M Innovative Properties Company | Emulsion polymerization of fluorinated monomers |
AU2002311389B2 (en) * | 2001-12-13 | 2008-01-31 | Rohm And Haas Company | Crosslinkable composition |
US6890360B2 (en) | 2001-12-17 | 2005-05-10 | 3M Innovative Properties Company | Fluorochemical urethane composition for treatment of fibrous substrates |
KR20050014834A (ko) * | 2002-05-24 | 2005-02-07 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 퍼플루오로폴리에테르 및 연장제를 포함하는 섬유 기질처리용 플루오로화합물 조성물 |
US7425279B2 (en) * | 2002-05-24 | 2008-09-16 | 3M Innovative Properties Company | Fluorochemical composition for treatment of a fibrous substrate |
CN100540586C (zh) * | 2002-05-24 | 2009-09-16 | 3M创新有限公司 | 含有氟化聚合物的含氟化合物组合物和利用其处理纤维底物 |
MXPA04011448A (es) * | 2002-05-24 | 2005-03-23 | 3M Innovative Properties Co | Composicion fluoroquimica para el tratamiento de un substrato fibroso. |
WO2005049744A1 (en) * | 2003-11-12 | 2005-06-02 | E.I. Dupont De Nemours And Company | Inkjet ink, ink set and method of printing |
US7541397B2 (en) * | 2006-03-10 | 2009-06-02 | Basf Corporation | Uretonimine-modified isocyanate composition and method of forming the same |
US7504523B2 (en) * | 2006-03-10 | 2009-03-17 | Basf Corporation | Uretonimine-modified isocyanate composition and method of forming the same |
US20080116414A1 (en) * | 2006-11-22 | 2008-05-22 | 3M Innovative Properties Company | Fluorochemical composition for treatment of a fibrous substrate |
CN101679705B (zh) | 2007-06-08 | 2013-12-11 | 3M创新有限公司 | 含氟烷基的酯低聚物与聚碳二亚胺的共混物 |
WO2011109386A1 (en) * | 2010-03-02 | 2011-09-09 | Ppg Industries Ohio, Inc. | One-component, ambient curable waterborne coating compositions, related methods and coated substrates |
AU2013351465A1 (en) | 2012-11-28 | 2015-03-05 | Evonik Industries Ag | New type of road markings for supporting the environment detection of vehicles |
DE102013206116A1 (de) | 2013-04-08 | 2014-10-09 | Evonik Industries Ag | Neuartige Straßenmarkierungen zur Unterstützung der Umfeldwahrnehmung von Fahrzeugen |
EP3936577A4 (de) | 2019-03-05 | 2022-12-28 | Nisshinbo Chemical Inc. | Vernetzungsmittel für wässrige harze, flüssigkeit mit vernetzungsmittel für wässrige harze und wässrige harzzusammensetzung |
KR102219875B1 (ko) * | 2019-10-07 | 2021-02-24 | 공주대학교 산학협력단 | 소각용 액체 연료 분무 인젝터 |
JP7413771B2 (ja) | 2019-12-25 | 2024-01-16 | 日清紡ケミカル株式会社 | 水性樹脂用架橋剤組成物および水性樹脂組成物 |
Citations (1)
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FR1469946A (fr) * | 1965-02-25 | 1967-02-17 | Bayer Ag | Procédé de préparation de carbodiimides |
Family Cites Families (9)
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DE1005726B (de) * | 1955-10-26 | 1957-04-04 | Bayer Ag | Stabilisierendes Mittel gegenueber den Einfluessen von Waerme und Feuchtigkeit in durch polysocyanate modifizierten Polyestermassen |
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FR1310138A (de) * | 1960-12-02 | 1963-03-06 | ||
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DE1190176B (de) * | 1961-04-25 | 1965-04-01 | Bayer Ag | Verwendung von Carbodiimiden gemeinsam mit siliciumorganischen Verbindungen als stabilisierende Mittel in estergruppenhaltigen Polyurethanen |
US3639353A (en) * | 1970-03-20 | 1972-02-01 | Goodrich Co B F | Polymers crosslinked with polycarbodiimides |
US3929733A (en) * | 1974-10-02 | 1975-12-30 | Upjohn Co | Polycarbodiimides from 4,4{40 -methylenebis(phenyl isocyanate) and certain carbocyclic monoisocyanates |
DE2536493A1 (de) * | 1975-08-16 | 1977-02-24 | Bayer Ag | Polymerisationsprodukte |
DE2624198C2 (de) * | 1976-05-29 | 1984-10-04 | Bayer Ag, 5090 Leverkusen | Polymerisationsprodukte |
-
1983
- 1983-02-24 US US06/469,434 patent/US4487964A/en not_active Expired - Fee Related
-
1984
- 1984-02-03 CA CA000446741A patent/CA1213394A/en not_active Expired
- 1984-02-23 EP EP84101922A patent/EP0120305B1/de not_active Expired
- 1984-02-23 JP JP59031572A patent/JPS59193916A/ja active Granted
- 1984-02-23 KR KR1019840000874A patent/KR900008527B1/ko not_active IP Right Cessation
- 1984-02-23 DE DE8484101922T patent/DE3460449D1/de not_active Expired
- 1984-02-23 AT AT84101922T patent/ATE21386T1/de active
- 1984-02-23 AU AU24864/84A patent/AU559037B2/en not_active Ceased
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FR1469946A (fr) * | 1965-02-25 | 1967-02-17 | Bayer Ag | Procédé de préparation de carbodiimides |
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5225519A (en) * | 1989-05-26 | 1993-07-06 | Industrie Vernici Italiane S.P.A. | Quick-hardening coating composition |
WO1990014371A1 (en) * | 1989-05-26 | 1990-11-29 | Industrie Vernici Italiane S.P.A. | A quick-hardening coating composition |
EP0449143A2 (de) * | 1990-03-23 | 1991-10-02 | UNION CARBIDE CHEMICALS AND PLASTICS COMPANY INC. (a New York corporation) | Bei niedrigen Temperaturen aktive aliphatische/aromatische Polycarbodiimide |
EP0449143A3 (en) * | 1990-03-23 | 1992-04-22 | Union Carbide Chemicals And Plastics Company Inc. (A New York Corporation) | Low temperature active aliphatic/aromatic polycarbodiimides |
US5360933A (en) * | 1991-12-26 | 1994-11-01 | Nisshinbo Industries, Inc. | Tetramethylxylylene carbodiimide |
EP0548815A3 (en) * | 1991-12-26 | 1993-09-29 | Nisshinbo Industries, Inc. | Polytetramethylxylylene carbodiimide |
EP0548815A2 (de) * | 1991-12-26 | 1993-06-30 | Nisshinbo Industries, Inc. | Tetramethylxylylene Carbodiimide |
US5349087A (en) * | 1992-04-29 | 1994-09-20 | E. I. Du Pont De Nemours And Company | Carbodiimides and processes therefor |
US5352400A (en) * | 1992-04-29 | 1994-10-04 | E. I. Du Pont De Nemours And Company | Carbodiimides and processes therefor |
EP0582983A1 (de) * | 1992-08-10 | 1994-02-16 | Nisshinbo Industries, Inc. | Verfahren zur Polycarbodiimidharzherstellung |
DE19529631C5 (de) * | 1994-08-11 | 2012-05-03 | Nisshinbo Industries, Inc. | Verwendung eines oberflächenaktiven Mittels zur Oberflächenbehandlung von Verstärkungsmaterial, Verstärkungsmaterial mit einer mit dem genannten oberflächenaktiven Mittel behandelten Oberfläche und Verwendung des Verstärkungsmaterials |
EP0963283B2 (de) † | 1997-01-31 | 2010-12-08 | Magna Interior Systems Inc. | Verfahren zum herstellen von dekorativen kraftfahrzeuginnenverkleidungen mit vollständiger und lichtstabiler polyurethanelastomerbeschichtung |
CN108003313A (zh) * | 2017-12-21 | 2018-05-08 | 上海朗亿功能材料有限公司 | 一种嵌段型聚碳化二亚胺水性交联剂及其制备方法 |
CN108003313B (zh) * | 2017-12-21 | 2020-08-04 | 上海朗亿功能材料有限公司 | 一种嵌段型聚碳化二亚胺水性交联剂及其制备方法 |
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Publication number | Publication date |
---|---|
DE3460449D1 (en) | 1986-09-18 |
KR850000484A (ko) | 1985-02-27 |
JPS6411051B2 (de) | 1989-02-23 |
CA1213394A (en) | 1986-10-28 |
AU559037B2 (en) | 1987-02-19 |
JPS59193916A (ja) | 1984-11-02 |
KR900008527B1 (ko) | 1990-11-24 |
AU2486484A (en) | 1984-08-30 |
EP0120305B1 (de) | 1986-08-13 |
ATE21386T1 (de) | 1986-08-15 |
US4487964A (en) | 1984-12-11 |
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